This invention relates to polyhydroindan carboxaldehydes and uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles and colognes.
Inexpensive chemical compositions of matter which can provide fresh, eucalyptus-like, balsamic, green, piney, ozoney, twiggy, woody and cinnamon-like aromas with green and twiggy, morning forest-like undertones are highly desirable in the art of perfumery. Many of the natural materials which provide such fragrances and contribute such desired nuances are high in cost, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
In the course of the last twenty years particularly, an increasing amount of attention has been devoted to the preparation and utilization of artifical perfuming and odor modifying agents possessing the skeleton of tricyclo[5.2.1.0.sub.2,6]decane. This attention has been stimulated mainly by an increased availability of cyclopentadiene, methylcyclopentadiene and the dimers thereof.
Thus, for example, U.S. Pat. No. 3,981,892 issued on Sept. 21, 1976 discloses the compounds defined according to the structure: ##STR7## wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond for use in perfumery. German Pat. No. 1617021 shows the compounds defined according to the structure: ##STR8## wherein R represents an acyl group or a hydrogen atom as possessing a perfuming note reminiscent of that developed by lavender oil. According to published Dutch Application No. 69/01750 the polycyclic gamma, delta-unsaturated aldehyde having the formula: ##STR9## develops a green-fruity character which is reminiscent of the Lily of the Valley fragrance.
U.S. Pat. No. 3,446,755 issued on May 27, 1969 discloses perfume compositions relating to synthetic spike lavender oil which include as a key ingredient one or both of compounds defined according to the generic structure: ##STR10## wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represent a carbon-carbon single bond.
The use of 4,7-methanoindene derivatives defined according to the structures: ##STR11## wherein one of the dashed lines in each of the molecules is a carbon-carbon double bond and the other of the dashed lines in each of the molecules is a carbon-carbon single bond is disclosed for use in perfumery (having odors which recall the odor of cardamon seed oil) in U.S. Pat. No. 3,417,132 issued on Dec. 17, 1968.
U.S. Pat. No. 4,275,251 issued on June 23, 1981 discloses the use of a genus of compounds defined according to the structure: ##STR12## wherein one of R.sub.1 " or R.sub.2 " represents methyl and the other of R.sub.1 " or R.sub.2 " represents hydrogen; wherein one of R.sub.4 " R.sub.5 " and R.sub.6 " represents methyl and the other of R.sub.4 " R.sub.5 " and R.sub.6 " represent hydrogen; wherein Y represents one of the moieties: ##STR13## wherein R.sub.3 " represents hydrogen, C.sub.1 -C.sub.3 acyl; C.sub.3 -C.sub.4 alkyl; C.sub.3 or C.sub.4 alkenyl or carbo-C.sub.1 -C.sub.3 alkoxy for use in augmenting or enhancing the aroma of perfume compositions or perfumed articles.
Furthermore, other oxygenated compounds having a bicyclopentadiene nuclus are known in the prior art and uses in perfumery thereof are known. Thus, for example, Kheisets and Virezub at Chem.Abstracts, Volume 61:8199c (abstract of Zh.Obshch. Khim. 34 (6) 2081-4) discloses for use in perfumery the compound defined according to the structure: ##STR14##
Zeinalov, et al at Chem. Abstracts 68, 49319d discloses the genus defined according to the structure: ##STR15## wherein R represents methyl, n-propyl or n-butyl.
Opdyke in Chem. Abstracts 92:11070y (Abstract of Food, Cosmet. Toxicol. 1976, 14, Suppl. 889) discloses the compound having the structure: ##STR16## in fragrance raw materials as well as its toxicological properties.
The compound having the structure: ##STR17## is disclosed in U.K. Patent specification No. 815,232 issued on June 24, 1959.
Furthermore, the compound having the structure: ##STR18## has been in use in the perfume industry for the past ten years and is known as "CYCLAPROP".
German Offenlengungsschrift No. 2,642,519 published on Mar. 23, 1978 and abstracted in Chem. Abstracts, 91:56477g discloses for use in perfumery the compounds having the structures: ##STR19## and the genus defined according to the structure: wherein R.sub.7 is alkyl or alkenyl.
The genus defined according to the structure: ##STR20## is disclosed at Chem. Abstracts, Volume 72:21406p (Abstract of of South African Patent No. 68/04722. The perfume use of the genus defined according to the structure: ##STR21## is set forth in Netherlands Published Application No. 76/08839 and German Offenlengungsschrift No. 2,623,285 published on Nov. 29, 1977. The genus defined according to the structure: ##STR22## as indicated in Dutch Published Application No. 76/08839 to be produced by means of an oxo reaction of 2 moles of carbon monoxide and hydrogen on one mole of dicyclopentadiene followed by partial hydrogenation.
Other oxo reaction products produced useful in perfumery are disclosed, for example, in U.S. Pat. No. 3,985,769 issued on Oct. 12, 1976, for example, the compound defined according to the structure: ##STR23## produced according to the reaction: ##STR24##
Nothing in the prior art however, discloses the polyhydroindan carboxaldehydes of our invention or mixtures of polyhydroindan carboxaldehydes of our invention or their organoleptic properties.